
Historic Route 66 Kid friendly Vacations
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Top Kid friendly vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥321,722, price is now ¥261,166 per person
¥261,166
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
It is a 1/2 a block off of Michigan Ave. and Ontario, terrific location. There was no carpet in the entire building which made it feel so much cleaner! Very modern rooms and lobby. The roof top bar was great. Staff at the rooftop bar were great too! The lobby staff were fantastic!!!! Always happy, trying to help without even being asked!!! Fantastic!!! Breakfast staff needed to relax a little bit. We were a party of 12, with 6 rooms. We were never allowed to even get a table of 4 so we could sit together. We could have been given tables at least by each other. They were not interested in accommodating us. Really felt like herding animals. Breakfast was good, lots of choices.
Reviewed on Sep 29, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥497,763, price is now ¥379,929 per person
¥379,929
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025

The Emily Hotel
Downtown Chicago
Price was ¥356,734, price is now ¥288,542 per person
¥288,542
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on Sep 29, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥326,296, price is now ¥268,442 per person
¥268,442
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on Sep 26, 2025

DoubleTree by Hilton St. Louis Forest Park
Central West End
Price was ¥428,178, price is now ¥355,120 per person
¥355,120
per person
Nov 16 - Nov 21
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to St. Louis (STL)
8.2/10 Very Good! (1,006 reviews)
Welcoming staff and beautiful location
Reviewed on Sep 27, 2025
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View all trips5* Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥497,763, price is now ¥379,929 per person
¥379,929
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025

Four Seasons Hotel St Louis
Downtown St. Louis
Price was ¥862,455, price is now ¥781,328 per person
¥781,328
per person
Nov 16 - Nov 21
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to St. Louis (STL)
9.4/10 Exceptional! (1,000 reviews)
Great help and classy property
Reviewed on Sep 22, 2025

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View all trips3 Night Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥366,658, price is now ¥298,221 per person
¥298,221
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
It is a 1/2 a block off of Michigan Ave. and Ontario, terrific location. There was no carpet in the entire building which made it feel so much cleaner! Very modern rooms and lobby. The roof top bar was great. Staff at the rooftop bar were great too! The lobby staff were fantastic!!!! Always happy, trying to help without even being asked!!! Fantastic!!! Breakfast staff needed to relax a little bit. We were a party of 12, with 6 rooms. We were never allowed to even get a table of 4 so we could sit together. We could have been given tables at least by each other. They were not interested in accommodating us. Really felt like herding animals. Breakfast was good, lots of choices.
Reviewed on Sep 29, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥362,687, price is now ¥302,136 per person
¥302,136
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on Sep 26, 2025

The Emily Hotel
Downtown Chicago
Price was ¥354,432, price is now ¥302,633 per person
¥302,633
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on Sep 29, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Historic Route 66
View all trips4 Night Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥321,722, price is now ¥261,166 per person
¥261,166
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
It is a 1/2 a block off of Michigan Ave. and Ontario, terrific location. There was no carpet in the entire building which made it feel so much cleaner! Very modern rooms and lobby. The roof top bar was great. Staff at the rooftop bar were great too! The lobby staff were fantastic!!!! Always happy, trying to help without even being asked!!! Fantastic!!! Breakfast staff needed to relax a little bit. We were a party of 12, with 6 rooms. We were never allowed to even get a table of 4 so we could sit together. We could have been given tables at least by each other. They were not interested in accommodating us. Really felt like herding animals. Breakfast was good, lots of choices.
Reviewed on Sep 29, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥497,763, price is now ¥379,929 per person
¥379,929
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on Sep 28, 2025

The Emily Hotel
Downtown Chicago
Price was ¥356,734, price is now ¥288,542 per person
¥288,542
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on Sep 29, 2025
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.